α,β-Unsaturated acetylenic γ-hydroxyketones have been shown to react with ethyl acetoacetate in a Michael-addition fashion and subsequently undergo cyclization followed by dehydration to give substituted furans with a predictable regiospecificity. The yields were good to excellent. A mechanism for the transformation is proposed, and this mechanism explains why furan formation does not take place when the same unsaturated ketones are treated with α-methylated acetoacetate and diethyl malonate.
Bibliographical noteSupplementary materials are available for this article. Go to the publisher’s online edition of Synthetic Communications1 for the following free supplemental resource: Full experimental and spectral details.
- Conjugated acetylenic ketones
- Propargylic alcohols
Sydnes, L. K., Isanov, R., Sengee, M., & Livi, F. (2013). Regiospecific Synthesis of Tetra-Substituted Furans. Synthetic Communications, 43(21), 2898-2905. https://doi.org/10.1080/00397911.2012.748076